(S)-1-(2,3-Dihydroxypropyl)cytosine
4-amino-1-[(2S)-2,3-dihydroxypropyl]pyrimidin-2-one
Product summary
Quick view
- Product family
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- Chemical Name
- 4-amino-1-[(2S)-2,3-dihydroxypropyl]pyrimidin-2-one
- MF
- C7H11N3O3
- MW
- 185.18
- Purity
- >=98%
(S)-1-(2,3-Dihydroxypropyl)cytosine is the unprotected (S)-GNA (glycol nucleic acid) cytosine nucleoside: a cytosine joined at N1 to an acyclic (S)-2,3-dihydroxypropyl "glycol" backbone in place of a ribose or deoxyribose sugar. CHEMOS lists it as catalog CH70002 with CAS 55559-70-1, molecular formula C7H11N3O3, and molecular weight 185.18 (PubChem CID 11805434; InChIKey LTTDCEYZEHQDGW-YFKPBYRVSA-N).
This is the parent glycol-cytosine unit: protecting the base and differentiating the two backbone hydroxyls yields the (S)-GNA-C phosphoramidite used to add a GNA cytosine during solid-phase oligonucleotide synthesis. According to PubMed, glycol nucleic acid is an acyclic nucleic-acid analog joined by phosphodiester bonds that is incorporated into oligonucleotides via phosphoramidite chemistry, and an (S)-GNA nucleotide increases resistance to nuclease degradation while having little impact on duplex structure.
Synonyms
(S)-GNA-C; 1-[(S)-2,3-dihydroxypropyl]cytosine; (S)-glycol cytosine nucleoside
Identity and specifications
| Catalog No. | CH70002 |
| CAS No. | 55559-70-1 |
| Molecular Formula | C7H11N3O3 |
| Molecular Weight | 185.18 |
| PubChem CID | 11805434 |
| InChIKey | LTTDCEYZEHQDGW-YFKPBYRVSA-N |
| Backbone | (S)-GNA (glycol nucleic acid), unprotected cytosine |
| Purity | >=98% |
Technical attributes
- Material class
- (S)-GNA nucleoside
- Nucleobase
- Cytosine
- Backbone scaffold
- (S)-2,3-dihydroxypropyl
- Protection state
- Unprotected
- Packaging
- 10 mg; 25 mg; 50 mg; 100 mg; Custom packaging on request
Application context
- Parent (S)-GNA-C nucleoside: the plain glycol-cytosine unit from which the base-protected monomer and (S)-GNA-C phosphoramidite are prepared.
- Acyclic backbone unit: the (S)-2,3-dihydroxypropyl glycol replaces the sugar ring, the defining feature of a GNA nucleotide.
- Nuclease-resistance research: according to PubMed, (S)-GNA incorporation has been studied for increasing resistance to exonuclease/phosphodiesterase degradation in siRNA duplexes.
Related technical resources
Oligonucleotide Modification
Sugar, base, backbone, terminal, and conjugation modifications for ASO, siRNA, guide RNA, aptamer, and research or labeling oligo projects.
Oligonucleotide Synthesis
Support for modified monomers, supports, sulfurizing reagents, cap analogs, and related oligo synthesis inputs.
Public references
- Sustainability Challenges and Opportunities in Oligonucleotide Manufacturing
Journal of Organic Chemistry, 2021
Product-family technical context
- Solid-phase supports for oligonucleotide synthesis
Current Protocols in Nucleic Acid Chemistry, 2013
Product-family technical context
- Deoxynucleoside phosphoramidites—A new class of key intermediates for deoxypolynucleotide synthesis
Tetrahedron Letters, 1981
Product-family technical context
- Synthesis of deoxyoligonucleotides on a polymer support
Journal of the American Chemical Society, 1981
Product-family technical context
- PubChem Compound 11805434
PubChem · CID 11805434
Frequently Asked Questions
How does an (S)-GNA cytosine differ from a normal cytidine?
In place of the ribose/deoxyribose sugar ring, the cytosine sits on an acyclic (S)-2,3-dihydroxypropyl (glycol) backbone. This is the defining feature of glycol nucleic acid (GNA), a simplified acyclic nucleic-acid analog joined by phosphodiester bonds.
What is this compound used to make?
It is the parent (S)-GNA cytosine nucleoside: protecting the base and differentiating the two backbone hydroxyls into dimethoxytrityl and phosphoramidite handles gives the (S)-GNA-C phosphoramidite used to add a GNA cytosine during oligonucleotide synthesis.
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